Gmail power tips, tools: Get the most from Google's e-mail

A long time ago, most people who used webmail were cybercafe-frequenting, patchouli-scented trustafarians backpacking through Europe. Just about everybody else used a real e-mail client that ran on the desktop.

But times change. With Google's launch of Gmail in 2004, webmail became powerful enough to replace a desktop client. Since then, Microsoft's Hotmail and Yahoo Mail have added features to catch up, but Gmail is still my favorite; I've been using it as my primary work and personal e-mail for most of the past three years.

It's also the favorite of many other home and business users. Gmail had 49 million users in September, according to comScore, making it the second-most-popular webmail service behind Yahoo Mail. What's more, Gmail is built into Android smartphones, so it's a natural for Android users.

Gmail is powerful and flexible, but not everybody's using it to its full advantage. You can beef it up by applying these tips and tools to customise and extend it.

Priority Inbox is a great new feature from Gmail that uses algorithms to determine which e-mails in your in-box are most important. It works very much like a spam filter. Priority Inbox looks for similarities between a new incoming message and messages you've received in the past. If the new e-mail is similar to messages you've previously read and replied to, Gmail filters the message into the Priority Inbox.

If new e-mail resembles messages you've ignored, Gmail figures it isn't as important and leaves it in your regular in-box.

Priority Inbox is a great feature because it saves you time sifting through e-mail. Your most important messages bubble to the top of your in-box, where you can give them immediate attention. Less important mail drifts down lower in your in-box, where you can deal with it when you have time.

You can activate and customise Priority Inbox by clicking Settings --> Priority Inbox; from there, you can tailor your Priority Inbox sections, train Priority Inbox to recognise messages important to you and more. See my recent blog post for some tips for using Priority Inbox, along with a look at some refinements that might be coming for the feature.

Switch off threaded conversations

By default, Gmail groups together all messages with the same subject line; Gmail figures they're all part of the same conversation. Messages with identical subject lines are hidden under the most recent message; click it to see the rest.

The conversations view was a revolutionary feature when Gmail launched, and also divisive -- some users (including me) love it, while others can't stand it. Opponents say that it's too difficult to separate unread messages in a thread from new messages that they haven't read yet; they have to wade through already-read messages to find the new e-mails.

Google threw a bone to the haters in September and gave users a setting to switch off conversations. Here's how to do it: Go to Settings --> General --> Conversation View to switch conversations on and off.

Gmail: Conversations on and off

Hate the conversations view (shown at top)? Switch it off (bottom).

Google Apps administrators will need to activate the "Enable pre-release features" option in the Google Apps control panel to allow users to switch between conversations and an unthreaded view (more on how to do that later in the story).

Get incoming mail notifications

Desktop e-mail software includes signals to let you know when you have new mail, by playing a sound or displaying a pop-up notifier. Google's free Google Notifier does the same thing for Gmail. It runs on your desktop and lets you know when you have new mail.

It can also set your default desktop e-mail program to Gmail, so if you click an e-mail address in a Web page or document, the action starts a new mail message in Gmail. And Google Notifier will warn you about upcoming Google Calendar meetings too.

Unfortunately, it can't be configured to show you only new Priority Inbox messages; it shows you all new messages in your in-box.

Use the Authentication icon for verified senders

This tip can save you from major security headaches: Gmail can be configured to show a special icon next to e-mail coming from eBay and PayPal to verify that the e-mail is legitimate and comes from the sender it appears to be from. This will help protect you from being phished. To activate the feature, go to Settings --> Labs and enable "Authentication icon for verified senders."

Customise the user interface

Gmail Labs is the place where Google lets you enable experimental Gmail features. It has a number of goodies to customise the user interface and streamline mail reading. A few of my favorites that I recommend enabling:

Add a "Mark as Read" button to the row of buttons at the top of Gmail, so you can mark a message as read without opening it. Otherwise, you'd have to click the "More Actions" menu to do the same thing; I'm exhausted just thinking about the extra work entailed.

Add a "Send & Archive" button to the outgoing message composition window, to send your reply to a message and archive the conversation in one click. Before the availability of this feature, Gmail users had to send e-mail, then archive the conversation by clicking separately. How did we ever bear it?

View multimedia content inline in your e-mail. Enable "Flickr previews in mail," "Google Maps previews in mail," "Picasa previews in mail," and "Yelp previews in mail" to view the content of links to those services inline in your mail messages. Similarly, Google Voice users will want to enable "Google Voice player in mail" to listen to their Google Voice messages in e-mail.

Explore other features of Labs

Labs has a wealth of other features; it's well worth browsing. Some more of my favorites:

* "Default 'reply to all' " makes "reply to all" the default option when replying to messages, rather than "reply to sender" being the default.

* "Got the wrong Bob?" warns you if it thinks you've misaddressed a message.

* "Auto-Advance" changes the default action when you delete, archive or mute a conversation. Instead of returning to your in-box, which is the default behavior, Gmail instead opens the next conversation, saving you a click.

* "Sender Time Zone" tells you what time it is at the location the sender sent the message from.

Use third-party add-ons

You can add even more power to Gmail by using third-party services that integrate with Gmail.

Rapportive

Rapportive, which runs in Chrome, Firefox, Safari and the Mailplane Gmail client, shows you a box of information about message senders, positioned next to e-mail messages. It can show you a picture of the sender (if it's available on the Web), as well as recent tweets and other social media activity. It's extremely handy when it comes to e-mails from strangers; it literally attaches a face to the e-mail address.

Rapportive works by cross-referencing the sender's e-mail address with online public databases such as Gravatar, Google Profiles, Twitter, RapLeaf, LinkedIn and more. (Users can also enter and update their own information with Rapportive.) If one of those services has a profile picture of the message sender, Rapportive displays that image next to the sender's e-mail, along with links to the sender's Twitter, LinkedIn and other social media pages.

Note: Rapportive is not always able to find information about a sender right away but usually does within a few minutes.

Rapportive says it uses only public information from those services. In other words, if your Facebook privacy settings say that only friends can see your Facebook profile picture, Rapportive won't show it to others in Gmail. But still, Rapportive might seem creepy to people who don't know how much information about them is public, so use it with caution (or, to be more candid, disclose that you're using it with caution).

For example, in January I had a business meeting with a woman who works outside the computer and technology industry. She was in the final weeks of work before going on maternity leave and was extremely pregnant. A few weeks ago, I heard from her again in e-mail, and Rapportive showed me her profile, along with a picture of her with her baby. I started to reply with a note that she and her baby looked great -- but then I thought to myself, "This woman isn't immersed in the Internet and social media as I am; if I tell her I've seen this picture, it will just alarm her unnecessarily." So I held back.

Boomerang

Boomerang for Gmail from Baydin lets you schedule e-mail to send later. It installs as an extension in Firefox or Chrome and adds a big "Send Later" button to the top of your compose window. Use it to schedule e-mail to go out in an hour, or tomorrow, or next month -- anytime in the future, even if your computer is offline or shut down completely.

To use Boomerang, you need to give the service access to your Gmail account. The company says it only accesses headers, but technically could access entire messages. And in some circumstances even message headers can contain sensitive information. So you'll want to be careful using Boomerang with sensitive information or in regulated environments.

Boomerang is currently in beta and requires an invitation to try it out, but you can sign up for an invitation online or follow @baydinsoftware on Twitter and tweet that you want an invitation; the developers say they'll direct-message you an invitation code within a day.

Mailplane

Mailplane is a fully functional Gmail client for the Mac only. It's a Web browser that's customised for use only with Gmail; it doesn't have an address bar, and you can't use it to open any Web sites other than Gmail. That means Gmail is always open on your desktop, and if you have multiple Gmail and Google Apps accounts, you can stay logged into an unlimited number of them simultaneously.

Mailplane lets you access your Mac OS X address book for sending mail, integrates with iPhoto and more. It has its own built-in notifier, but unlike Google Notifier, Mailplane can be configured to only show you new messages in your Priority Inbox.

I use Mailplane as my primary mail client. It costs $24.95, and you can try it for free for 30 days.

Power tips

Use your own domain with Gmail

You don't have to have an @gmail.com address to use Gmail. Sign up for Google Apps, and you can use Gmail's webmail client with your own domain. The Standard Edition is free and supports up to 50 users. It's great for individual users and small businesses (it's the plan I use).

The Premier Edition starts at $50 per user account per year and supports added features, including unlimited users and increased storage. (Regular Gmail accounts and the mail service in Google Apps Standard Edition support 7GB per user, while the Premier Edition supports up to 25GB.) In addition to Gmail, you get other Google Apps with your own domain, including Google Calendar, Google Groups and Google Docs.

Aggregate mail from multiple accounts

Sick of checking multiple in-boxes, possibly in different e-mail clients, to keep up with all your e-mail accounts? Send all your e-mail to Gmail instead. Go to Settings --> Accounts --> "Get mail from other accounts" or "Check mail using POP3," depending on which version of Gmail you're using. Enter the e-mail address and POP3 address of the remote server you want to check. (Not an IT pro? You can get that information from your e-mail administrator or from your Internet service provider's configuration instructions.)

Warning: Aggregating your employer's e-mail into Gmail could violate security policies and confidentiality regulations. If you're an end user, check with your IT manager for permission, and if you're an IT manager, check with your company's compliance officers.

Gmail will occasionally poll the external server for new messages. The more frequently you get mail on that server, the more frequently Gmail will poll. You can speed things up even more by going to Settings --> Labs and enabling "Refresh POP accounts"; that adds a link to the top of your Gmail that allows you to poll external POP servers manually.

Gmail aggregation works with other webmail services if those services also support POP. Hotmail does, as does the premium version of Yahoo Mail, but not the free, basic Yahoo Mail.

Use remote servers to send mail

When you have Gmail checking mail from remote servers, you can also configure Gmail to send mail using your e-mail address on that remote server. Configure that by going to Settings --> Accounts --> Send mail as.

If you do that, it'll be obvious to the recipient on some e-mail systems, with a glance at the "From" address, that the message came from Gmail and not the remote server -- it will say something like "<my Gmail address> on behalf of <my alternate address>" or "<my alternate address> (sent by <my Gmail address>)." In other cases, your recipient will be able to see your Gmail address by examining the e-mail headers.

Gmail sent from another e-mail address's SMTP server

To solve that problem, you can configure Gmail to use the remote address's SMTP server to send the e-mail. Get the remote SMTP address when you get the POP3 address, and configure both at the same time.

Warning: As with the previous tip, don't attempt to use your employer's SMTP server without getting permission first. Many IT administrators will have blocked this option for an enterprise system.

In Gmail, go to Settings --> Accounts --> Send mail as. If you're setting up a new "Send mail as" address, click "Send mail from another address" or "Add another email address you own," depending on which version of Gmail you're using. If you're editing an existing address, locate that address in the list and then click "Edit info." Either way, once you've gotten started on the configuration, just follow the instructions in the wizard to finish.

Aggregate mail for multiple domains

With Google Apps, you can aggregate e-mail from multiple domains. This is better than fetching it remotely; it's faster because incoming e-mail goes directly to your Google Apps account. Also, you don't have to mess with SMTP settings. To configure, go to Settings --> Manage this domain --> Domain settings --> Domain names, and follow the instructions to add a domain.

This is handy for companies that do business under multiple domains; people from different business units can have their own branded e-mail addresses and have it all go to the same Google Apps account.

Get new goodies faster on Google Apps -- if you dare

Google rolls out new and experimental Gmail features to individual Gmail users first, holding them back from Google Apps customers until later. Adventurous Google Apps administrators can get new features faster by digging into the Control Panel. Select Manage this domain --> Domain settings --> General --> New services and pre-release features. Check "Automatically add new services when they become available," and also check "Enable pre-release features." Also, under "Control Panel" select "Next generation (U.S. English only)."

Warning: These settings are deliberately buried to make sure users know they're getting access to experimental features. If you're not willing to run the risk of your e-mail getting wonky, just leave the default settings alone, and you'll get new Gmail features after they've been tested by other people. It's safer that way. On the other hand, I've had these settings activated for a long time and have never had a problem.

Using these tips and tools, you can make a powerful e-mail client even more so. Share your own favorite Gmail tips in the reader comments.

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